Comes from baseketball where players line up at the free throw line and tip it off the backboard consecutively, one after another.

Think of it in the sense of a group of men runnin a train on a woman. First man in line hits, next man follows until everyone has had a turn...

If the nelly song is the first time u have heard this term try listening to the lyrics more carefully. Just cause they say " it must be your ass cause its not your face" doesnt mean a tip drill is a chick with a big botty and an ugly face.

example:
"I said it ain't no fun less we all get some
I need a tipdrill, we need a tipdrill "

When a girl bends over and her man puts his penis in her ass crack without any penetration. This is usually done as foreplay before doggystyle sex or as an act when the man and the woman do not want to engage in full intercourse. It is the ass equivalant of a titty fuck. The woman's ass cheeks are used to excite the penis, sometimes to ejaculation. Her ass is "polishing your tip".

ALSO, a girl who has a nice ass. This is because a girl needs a nice ass in order for this act to be pleasureable.

Many people confuse this word for the equivelent of running the train. This is because this act is used by many men on one woman on after the other. This is common because a tip drill does not involve penetration, making it easier to be repeated on one girl in a short amount of time.

The act is mock performed in Nelly's "Tip Drill" video. Also, the video focuses on the ass crack and at the end, Nelly swipes a credit card on a girl's ass, simulating the act.

"See now i wanna let you ride but the rubber might slide you's a tip drill girl you a tip drill"

The Urban Dictionary T-Shirt

a UGLY female that got a nice shape or jus a big ass and tha only rezon he wit her cuz she got a big ass or whatnot

a tip drill for a female iz:

a UGLY nigga who got money or who spend money on her..and thas the only rezon she with him

"I got you payin my bills and buyin automobiles
Yous a tipdrill, nigga you a tipdrill
I got you payin my bills and buyin automobiles
Yous a tipdrill, nigga you a tipdrill
I know you a trick go spend that shit
You old tipdrill, you monkeyass tipdrill"

The Urban Dictionary T-Shirt

During a lap dance a stripper will back that big b00ty up to grind n bounce her ass crack all ovah tha john's dick. Essentially this is a repetitive screwing like motion that drills tha nigga for a tip. The term can be used as a verb to describe the act, & as a noun to describe either the man or woman involved in this luscious freaky simulated sex act. Keep your mind on the money n the act as for the face who gives a damn what the trick or hoe looks like when drillin yer tip in that dark mine hole

Verb- shows action (action verb) or being (linking verb)

Nelly:
Turn that ass up mama put that dip in ya back
And let me tip drill, just let me tipdrill